Celebrate Halloween With Wine Tasting In Downtown Evansville

Downtown Evansville is serving up a night of spooky fun, great wine, and live entertainment this fall. The Spooky Wine Walk presented by Romain Cross Pointe happens Friday, October 3, 2025, from 5:30 to 8:30 PM along the 300, 400, and 500 blocks of Main Street.

Guests can expect wine, shopping, dining, and plenty of entertainment as Downtown transforms into a lively Halloween-themed destination. Costumes are encouraged, so bring your best witch hats and vampire capes for an evening under the October sky.

Wine, Cocktails, and More

This year’s event brings even more drink options. Guests will enjoy pours from Indiana wineries, including Hymn & Herd Winery, Two-EE’s Winery, and Whyte Horse Winery. In addition to wines, the 2025 lineup also features cocktails from Shake Up Cocktails, wine slushies, and mocktails from River City Coffee + Goods.

Each general admission ticket includes a commemorative tumbler and two drink tickets good for 4-ounce pours. Extra drink tickets will be available for purchase during the event.

Photo: TYMEALLO Studios

Entertainment and Activities

The Spooky Wine Walk isn’t just about the drinks. Guests will be treated to a full night of live entertainment and activities, including:

Fire performances lighting up Main Street
Henna tattoos from Mo Hall of First House Salon
Live music from MacroGeo, LaTasha Shemwell with Josh Orion, and The Prismatic Shards
Tarot readings with Sarah Pritchett Tarot
Live guest illustrations from Art by Faith
A spooky costume contest with prizes
Photo stations for capturing the night with friends

BlueBird Hot Chicken and Agape Graze will be on site, and guests can also explore more than 30 restaurants and bars in Downtown Evansville.

Wine Walk Passport and Prizes

Every ticket holder will receive a Wine Walk Passport at check-in. Guests who collect a stamp from each participating business can return their completed passport for a chance to win a gift basket filled with gift cards, Evansville merchandise, and goodies from our Downtown businesses.

Ticket Information

Advance tickets are $15 per person and include a commemorative tumbler and two drink tickets. Tickets at the event will be $25 per person. Availability is limited and the event often sells out, so buying tickets in advance is recommended.

Additional drink tickets will be available for $5 each, cash only, at the registration area.

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Event Details and Registration

Check-in begins at 5 PM on the 400 block of Main Street. Guests must be 21 or older to enjoy the wine, cocktails, and mocktails. A valid ID will be required at check-in.

Parking is available in more than 7,000 public and private spaces throughout Downtown, with free street parking after 5 PM. City parking garages at 500 Sycamore Street and at 3rd and Locust will also be open.

See How Downtown Evansville Has Changed Over the Years

I find looking back on the way things used to be fascinating. Don't get me wrong, I'm glad I'm living through the current time period. The conveniences of answering any question we have in seconds, or ordering practically anything we want or need and having it delivered to our doorstep is pretty sweet. But, there is something fun about seeing how things around us have evolved. As an Evansville native, and spending quite a bit of my time in downtown Evansville (that's where the station is located), I've always appreciated the older architecture of the buildings around the area. So, I dug into the Willard Library Archives to see how a few of those areas look now compared to then. Some have changed a little, others quite a bit, and a few don't even exist any more. Take a look.

Gallery Credit: Ryan O'Bryan

Source: Downtown Evansville’s Spooky Wine Walk Promises Wine, Costumes & Thrills

Categories: Owensboro – Daviess County News, What's New